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Pure Appl. Chem., 1996, Vol. 68, No. 6, pp. 1201-1205

http://dx.doi.org/10.1351/pac199668061201

Conformation of cyclic peptides. Principle concepts and the design of selectivity and superactivity in bioactive sequences by 'spatial screening'

H. Kessler, R. Gratias, G. Hessler, M. Gurrath and G. Müller

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  • Chatterjee Jayanta, Rechenmacher Florian, Kessler Horst: N -Methylierung von Peptiden und Proteinen: ein wichtiges Element für die Regulation biologischer Funktionen. Angew. Chem. 2013, 125, 268. <http://dx.doi.org/10.1002/ange.201205674>
  • Chatterjee Jayanta, Rechenmacher Florian, Kessler Horst: N -Methylation of Peptides and Proteins: An Important Element for Modulating Biological Functions. Angew. Chem. Int. Ed. 2013, 52, 254. <http://dx.doi.org/10.1002/anie.201205674>
  • Bochen Alexander, Marelli Udaya Kiran, Otto Elke, Pallarola Diego, Mas-Moruno Carlos, Di Leva Francesco Saverio, Boehm Heike, Spatz Joachim P., Novellino Ettore, Kessler Horst, Marinelli Luciana: Biselectivity of isoDGR Peptides for Fibronectin Binding Integrin Subtypes α5β1 and αvβ6: Conformational Control through Flanking Amino Acids. J. Med. Chem. 2013, 56, 1509. <http://dx.doi.org/10.1021/jm301221x>
  • Siodłak Dawid, Macedowska-Capiga Agnieszka, Broda Małgorzata A., Kozioł Anna E., Lis Tadeusz: The cis-trans isomerization of N -methyl-α,β-dehydroamino acids. Biopolymers 2012, 98, 466. <http://dx.doi.org/10.1002/bip.22082>
  • Malešević Miroslav, Schumann Michael, Jahreis Günther, Fischer Gunter, Lücke Christian: Design of Cyclic Peptides Featuring Proline Predominantly in the cis Conformation under Physiological Conditions. ChemBioChem 2012, 13, 2122. <http://dx.doi.org/10.1002/cbic.201200366>
  • Angelici Gaetano, Castellucci Nicola, Tomasini Claudia: Conformational studies on a medium size cyclopseudopeptide containing the oxazolidin-2-one moiety. J. Phys. Org. Chem. 2012, 25, 965. <http://dx.doi.org/10.1002/poc.2977>
  • Ginotra Yamini P., Ramteke Shefali N., Srikanth Rapole, Kulkarni Prasad P.: Mass Spectral Studies Reveal the Structure of Aβ1–16–Cu2+ Complex Resembling ATCUN Motif. Inorg. Chem. 2012, 51, 7960. <http://dx.doi.org/10.1021/ic301244x>
  • Rutters Jochem P. A., Verdonk Yvette, de Vries Remko, Ingemann Steen, Hiemstra Henk, Levacher Vincent, van Maarseveen Jan H.: Synthesis of strained cyclic peptides via an aza-Michael–acyl-transfer reaction cascade. Chem. Commun. 2012, 48, 8084. <http://dx.doi.org/10.1039/c2cc34121b>
  • Frank Andreas O., Otto Elke, Mas-Moruno Carlos, Schiller Herbert B., Marinelli Luciana, Cosconati Sandro, Bochen Alexander, Vossmeyer Dörte, Zahn Grit, Stragies Roland: Konformative Kontrolle über Integrin-Subtyp-Selektivitäten in isoDGR-Peptidmotiven: ein biologischer Schalter. Angew Chem 2010, 122, 9465. <http://dx.doi.org/10.1002/ange.201004363>
  • Frank Andreas O., Otto Elke, Mas-Moruno Carlos, Schiller Herbert B., Marinelli Luciana, Cosconati Sandro, Bochen Alexander, Vossmeyer Dörte, Zahn Grit, Stragies Roland: Conformational Control of Integrin-Subtype Selectivity in isoDGR Peptide Motifs: A Biological Switch. Angew Chem Int Ed 2010, 49, 9278. <http://dx.doi.org/10.1002/anie.201004363>
  • Laufer Burkhardt, Frank Andreas O., Chatterjee Jayanta, Neubauer Thomas, Mas-Moruno Carles, Kummerlöwe Grit, Kessler Horst: The Impact of Amino Acid Side Chain Mutations in Conformational Design of Peptides and Proteins. Chemistry - A European Journal 2010, 16, 5385. <http://dx.doi.org/10.1002/chem.201000545>
  • KESSLER H., GRATIAS R., HESSLER G., GURRATH M., MUELLER G.: ChemInform Abstract: Conformation of Cyclic Peptides. Principle Concepts and the Design of Selectivity and Superactivity in Bioactive Sequences by Spatial Screening. ChemInform 2010, 28, no. <http://dx.doi.org/10.1002/chin.199706328>
  • Datta Shreya, Bucks Megan E., Koley Dipankar, Lim Pei Xin, Savinov Sergey N.: Functional profiling of p53-binding sites in Hdm2 and Hdmx using a genetic selection system. biorg med chem 2010, 18, 6099. <http://dx.doi.org/10.1016/j.bmc.2010.06.053>
  • Dong Maoqing, Narang Pooja, Pinon Delia I., Bordner Andrew J., Miller Laurence J.: Refinement of the pharmacophore of an agonist ligand of the secretin receptor using conformationally constrained cyclic hexapeptides. Peptides (Fayetteville) 2010, 31, 1094. <http://dx.doi.org/10.1016/j.peptides.2010.02.024>
  • Mayorov Alexander V., Cai Minying, Palmer Erin S., Liu Zhihua, Cain James P., Vagner Josef, Trivedi Dev, Hruby Victor J.: Solid-phase peptide head-to-side chain cyclodimerization: Discovery of C2-symmetric cyclic lactam hybrid α-melanocyte-stimulating hormone (MSH)/agouti-signaling protein (ASIP) analogues with potent activities at the human melanocortin receptors. Peptides (Fayetteville) 2010, 31, 1894. <http://dx.doi.org/10.1016/j.peptides.2010.06.026>
  • Beierle John M., Horne W. Seth, van Maarseveen Jan H., Waser Beatrice, Reubi Jean Claude, Ghadiri M. Reza: Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three&hyphen;Dimensional Scaffolds for Rational Drug Design: Receptor&hyphen;Selective Somatostatin Analogues. Angew Chem 2009, 121, 4819. <http://dx.doi.org/10.1002/ange.200805901>
  • Beierle John M., Horne W. Seth, van Maarseveen Jan H., Waser Beatrice, Reubi Jean Claude, Ghadiri M. Reza: Conformationally Homogeneous Heterocyclic Pseudotetrapeptides as Three-Dimensional Scaffolds for Rational Drug Design: Receptor-Selective Somatostatin Analogues. Angew Chem Int Ed 2009, 48, 4725. <http://dx.doi.org/10.1002/anie.200805901>
  • Juaristi Eusebio, Gentilucci Luca, Cardillo Giuliana, Tolomelli Alessandra, De Marco Rossella, Garelli Andrea, Spampinato Santi, Spartà Antonino: Synthesis and Conformational Analysis of Cyclotetrapeptide Mimetic β-Turn Templates and Validation as 3D Scaffolds. ChemMedChem 2009, 4, 517. <http://dx.doi.org/10.1002/cmdc.200800407>
  • Arbor Sage, Kao Jeff, Wu Yun, Marshall Garland R.: c[D-pro-Pro-D-pro-N-methyl-Ala] adopts a rigid conformation that serves as a scaffold to mimic reverse-turns. Biopolymers 2008, 90, 384. <http://dx.doi.org/10.1002/bip.20869>
  • Malešević Miroslav, Jahreis Günther, Wawra Stephan, Fischer Gunter, Lücke Christian: Conformational Consequences of Regio- and Stereoselective Disulfide Bridge Oxidation in a Cyclic Peptide. Chem Eur J of Chem Bio 2008, 9, 46. <http://dx.doi.org/10.1002/cbic.200700529>
  • Chatterjee Jayanta, Mierke Dale F., Kessler Horst: Conformational Preference and Potential Templates ofN-Methylated Cyclic Pentaalanine Peptides. Chem Eur J 2008, 14, 1508. <http://dx.doi.org/10.1002/chem.200701029>
  • Bisek Nicola, Wetzel Stefan, Arndt Hans-Dieter, Waldmann Herbert: Synthesis and Conformational Analysis of Stevastelin C3 Analogues and Their Activity Against the Dual-Specific Vaccina H1-Related Phosphatase. Chem Eur J 2008, 14, 8847. <http://dx.doi.org/10.1002/chem.200800692>
  • Jeremic Tatjana, Linden Anthony, Heimgartner Heinz: New 21- and 24-atom Aib-containing cyclopeptides. J Peptide Sci 2008, 14, 1051. <http://dx.doi.org/10.1002/psc.1041>
  • Gentilucci Luca, Squassabia Federico, Demarco Rossella, Artali Roberto, Cardillo Giuliana, Tolomelli Alessandra, Spampinato Santi, Bedini Andrea: Investigation of the interaction between the atypical agonist c[YpwFG] and MOR : The atypical opioid agonist c[YpwFG]. FEBS J 2008, 275, 2315. <http://dx.doi.org/10.1111/j.1742-4658.2008.06386.x>
  • Guthöhrlein E. W., Malešević M., Majer Z., Sewald N.: Secondary structure inducing potential of β-amino acids: Torsion angle clustering facilitates comparison and analysis of the conformation during MD trajectories. Biopolymers (Biospectroscopy) 2007, 88, 829. <http://dx.doi.org/10.1002/bip.20859>
  • Hall Pamela R., Malone LaDonna, Sillerud Laurel O., Ye Chunyan, Hjelle Brian L., Larson Richard S.: Characterization and NMR Solution Structure of a Novel Cyclic Pentapeptide Inhibitor of Pathogenic Hantaviruses. Chem Biol Drug Design 2007, 69, 180. <http://dx.doi.org/10.1111/j.1747-0285.2007.00489.x>
  • H?rger Rolf, Geyer Armin: A shape-persistent d,l-dipeptide building block for the assembly of rigidified oligopeptides. Org Biomol Chem 2006, 4, 4491. <http://dx.doi.org/10.1039/b613172g>
  • Jeremic Tatjana, Linden Anthony, Moehle Kerstin, Heimgartner Heinz: Synthesis and conformational analysis of 18-membered Aib-containing cyclohexapeptides. Tetrahedron 2005, 61, 1871. <http://dx.doi.org/10.1016/j.tet.2004.12.012>
  • Rayan Anwar, Senderowitz Hanoch, Goldblum Amiram: Exploring the conformational space of cyclic peptides by a stochastic search method. Mol Graph Model 2004, 22, 319. <http://dx.doi.org/10.1016/j.jmgm.2003.12.012>
  • Baldauf Carsten, G��nther Robert, Hofmann Hans-J��rg, Asakawa Naoki: Subject Index. Journal of Molecular Structure: THEOCHEM 2004, 675, 187. <http://dx.doi.org/10.1016/j.theochem.2003.12.029>
  • Loiseau Nicolas, Gomis Jean-Marie, Santolini Jérôme, Delaforge Marcel, André François: Predicting the conformational states of cyclic tetrapeptides. Biopolymers (Biospectroscopy) 2003, 69, 363. <http://dx.doi.org/10.1002/bip.10339>
  • Stöckle Matthias, Voll Georg, Günther Robert, Lohof Elisabeth, Locardi Elsa, Gruner Sibylle, Kessler Horst: Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid. Org Lett 2002, 4, 2501. <http://dx.doi.org/10.1021/ol026126d>
  • Leipert Dietmar, Nopper Dirk, Bauser Marcus, Gauglitz Günter, Jung Günther: Untersuchung der molekularen Erkennung von Aminosäuren durch Cyclopeptide mit reflektometrischer Interferenzspektroskopie. Angew Chem 1998, 110, 3503. <http://dx.doi.org/10.1002/(SICI)1521-3757(19981204)110:23<3503::AID-ANGE3503>3.0.CO;2-F>
  • Wessel Hans Peter, Banner David, Gubernator Klaus, Hilpert Kurt, Müller Klaus, Tschopp Thomas: 6-Guanidiniopyranosen — neuartige Peptidmimetika auf Kohlenhydratbasis. Angew Chem 1997, 109, 791. <http://dx.doi.org/10.1002/ange.19971090725>
  • Haubner Roland, Kessler I. Horst: Stereoisomere Peptid-Bibliotheken und Peptidmimetika zum Design von selektiven Inhibitoren des αv β3-Integrins für eine neuartige Krebstherapie. Angew Chem 1997, 109, 1440. <http://dx.doi.org/10.1002/ange.19971091304>
  • Koppitz Marcus, Huenges Martin, Gratias Rainer, Kessler Horst, Goodman Simon L., Jonczyk Alfred: Synthesis of Unnatural LipohilicN-(9H-Fluoren-9-ylmethoxy)carbonyl-Substituted α-Amino Acids and Their Incorporation into Cyclic RGD-Peptides: A structure-activity study. HCA 1997, 80, 1280. <http://dx.doi.org/10.1002/hlca.19970800423>
  • Mechnich Oliver, Messier Gerhard, Kessler Horst, Bernd Michael, Kutscher Bernhard: Cyclic Heptapeptides Axinastatin 2, 3, and 4: Conformational analysis and evaluation of the biological potential. HCA 1997, 80, 1338. <http://dx.doi.org/10.1002/hlca.19970800503>
  • Möhle Kerstin, Gußmann Martin, Hofmann Hans-Jörg: Structural and energetic relations between β turns. J Comput Chem 1997, 18, 1415. <http://dx.doi.org/10.1002/(SICI)1096-987X(199708)18:11<1415::AID-JCC8>3.0.CO;2-O>
  • Müller Annett, Schumann Frank, Koksch Mario, Sewald Norbert: Synthesis of cyclic RGD-peptides containing β-amino acids. Lett Peptide Sci 1997, 4, 275. <http://dx.doi.org/10.1007/BF02442889>
  • Müller Gerhard: Die β-Schleife als Selektivitätsschalter: βI oder βII′? – Das ist hier die Frage. Angew Chem 1996, 108, 2941. <http://dx.doi.org/10.1002/ange.19961082307>